Montaione Vacations from $580

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Your Montaione Vacation

When a break in the city is calling, answer it with a vacation package to Montaione. The neighborhood of Capannoli, which is great for walking, nature and history, makes an awesome base for your adventures. If your trip to Montaione includes some sightseeing, don't miss popular attractions like Castelfalfi Golf Course, Monastery of San Vivaldo and Teatro del Popolo. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Montaione vacation is simple with Expedia.

The Latest Montaione vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Fattoria degli Usignoli

Hotel Fattoria degli Usignoli

4 out of 5
Price was $753, price is now $580 per person
$580
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.2/10 Very Good! (158 reviews)
Absolutely beautiful property, quiet and peaceful!! Loved the experience!!

Reviewed on Oct 5, 2025

Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

4 out of 5
Historic Centre of Florence
Price was $1,209, price is now $880 per person
$880
per person
Jan 8 - Jan 14
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (999 reviews)
Wonderful hotel. Incredible views from the huge rooftop bar/pool deck. Wonderful breakfast buffet with many hot and cold options. Main level bar is beautiful and the seating areas are both well-appointed and comfortable. Both bars offer gratis snacks. View of the river Arno, Piazza el Michelangelo and more from our room window were stunning. You can literally walk almost anywhere in the city from this location.

Reviewed on Oct 18, 2025

Palazzo Lorenzo Hotel Boutique & Spa

Palazzo Lorenzo Hotel Boutique & Spa

4 out of 5
San Lorenzo
Price was $1,239, price is now $933 per person
$933
per person
Jan 8 - Jan 14
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (592 reviews)
Beautiful hotel, clean room beautifully decorated and with everything needed to make our stay feel luxurious and comfortable. Friendly helpful staff. Delicious buffet breakfast and free use of spa facilities. It felt 5 star!

Reviewed on Sep 27, 2025

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $1,437, price is now $1,091 per person
$1,091
per person
Jan 6 - Jan 11
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (56 reviews)
I cannot give this property and its staff enough credit! From our our excellent check-in with Elisa to any issues we’d need in the evening with, Jacobo, all of our needs were met. The chic, yet comfortable interiors were a breath of fresh air. The property and our bedroom were impeccable! I will recommend this hotel to my friends and family and will absolutely stay here agin!

Reviewed on Oct 21, 2025

25hours Hotel Florence Piazza San Paolino

25hours Hotel Florence Piazza San Paolino

4 out of 5
Historic Centre of Florence
Price was $1,177, price is now $908 per person
$908
per person
Jan 8 - Jan 14
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (895 reviews)
Great stay! Funky hotel decor, but great location and super easily walkable to everything.

Reviewed on Oct 15, 2025

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Discover the most popular places to visit in Montaione

Castelfalfi Golf Course

Enjoy a round of golf in Castelfalfi at Castelfalfi Golf Course. Discover the beautiful countryside in this relaxing area.

Castelfalfi Golf Course

Monastery of San Vivaldo

You can learn about the history of San Vivaldo with a trip to Monastery of San Vivaldo. Discover the beautiful countryside and wineries in this relaxing area.

Monastery of San Vivaldo

What to do in Montaione

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$138
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
San Gimignano: The Medieval City

San Gimignano: The Medieval City

$23
per adult
San Gimignano: The Medieval City
Wine tasting in San Gimignano

Wine tasting in San Gimignano

$35
per adult
Wine tasting in San Gimignano
See all activities in Montaione

Montaione Hotel Deals

Castelfalfi

Castelfalfi

5 out of 5
Loc. Castelfalfi, Montaione, FI
$611 nightly
The price is $684 total per night from Nov 19 to Nov 20
$684 total
Nov 19 - Nov 20
Total with taxes and fees
9.4/10 Exceptional! (154 reviews)
Our stay at Castelfalfi was nothing short of extraordinary. From the moment we arrived, the property’s breathtaking beauty was immediately evident. The views of the rolling Tuscan hills from the Olivo Restaurant and the spa pools are absolutely unparalleled – it’s a scene straight out of a dream. ...

Reviewed on Sep 22, 2025

Castelfalfi
Boccioleto Resort&Spa

Boccioleto Resort&Spa

4 out of 5
Via Collegalli, Montaione, FI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $106 total per night from Nov 12 to Nov 13
$106 total
Nov 12 - Nov 13
Total with taxes and fees
9.2/10 Wonderful! (112 reviews)
The staff was incredibly kind and accommodating. Our flight was delayed but they were very accommodating and held a table for us in the restaurant. They also made sure we had everything we needed. The room was a bit dated but the bed was comfortable.

Reviewed on Oct 19, 2025

Boccioleto Resort&Spa
Castellare di Tonda Resort & Spa

Castellare di Tonda Resort & Spa

Via Cerroni, Montaione, FI
7.8/10 Good! (49 reviews)
Great place to relax and recharge!
The reception was extremely helpful with all our queries even before we got to the property and really helped make sure we had a comfortable stay. The apartment came with amazing views and the basic necessities. The pool was a very nice size and kept clean for us to enjoy. We also booked a horse ...

Reviewed on Jul 28, 2020

Get rates
Castellare di Tonda Resort & Spa
See all 576 properties in Montaione
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Montaione Vacation Packages

Montaione Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
2,800
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Montegufoni Castle, Castello Sonnino and Castle of Oliveto

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Frequently asked questions

How much does a Montaione vacation package cost?
You can pick up a vacation package to this top destination from $580 on Expedia. However, how much your vacation to Montaione costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Montaione?
You can generally find lower rates and greater availability in September, November and December. Check out our cheap Montaione vacation packages and you could score some excellent off-season deals.
How many days is enough for Montaione?
With a well-organized schedule, you can easily visit the most popular Montaione attractions in a few days. But if you want to explore off the beaten track or take day trips, think about booking your Montaione vacation for longer.
Is it worth booking a vacation package to Montaione?
Montaione has all the ingredients you need for an amazing break — views, nature and hiking are just the start. Whether you'd like to visit attractions like Castelfalfi Golf Course and Monastery of San Vivaldo, or venture off the beaten track, you'll have plenty to see and do on your Montaione vacation.
How to find the best Montaione package deals?
Begin your search for a Montaione package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Montaione package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Montaione adventure off to a flying start.
Is it cheaper to book a Montaione vacation as a package?
You can enjoy significant savings on your next Montaione retreat by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Montaione?
If you have your Montaione travel dates locked in, book early to bag some unbeatable deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Montaione?

  1. Choose your travel dates: The things you want to do in Montaione and your preferred season can help you decide when to go.
  2. Set a budget: Factor in expenses such as food, flights and transportation when calculating how much to put aside for your trip to Montaione. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Explore Montaione using Expedia's trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Montaione. You can also save your favorite places, collaborate with family and friends and organize all your plans in one place.
  4. Decide how many days away: Start by compiling a list of the activities and sights you'd like to get to in Montaione. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the right Montaione vacation package for you.
  6. Book activities and experiences in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on Montaione's best offerings. Find all the fun things to do in Montaione with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Montaione vacation packages?
If you're like us, you love traveling the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Montaione break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.